二甲基对苯二胺二盐酸 → 5-苯基噻吩-2-羧酸

HRID 412005

反应方程式

HRID 412005 反应方程式
[C:1]1([C:7]2[S:11][C:10]([CH:12]=[O:13])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:14]P([O-])(O)=O.[K+].[O-]Cl=O.[Na+].[OH-].[Na+]>C1COCC1.CC(O)(C)C.O>[C:1]1([C:7]2[S:11][C:10]([C:12]([OH:14])=[O:13])=[CH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参与物

8

反应物 4

HCID 14798二甲基对苯二胺二盐酸HCID 1770535-苯基-2-噻吩甲醛HCID 516951磷酸钾HCID 23668197亚氯酸钠

产物 1

HCID 7364945-苯基噻吩-2-羧酸收率 51%

试剂、催化剂与溶剂 3

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂2 次HCID 6386叔丁醇溶剂HCID 8028四氢呋喃溶剂

实验过程

5-Phenylthiophene-2-carboxaldehyde (750 mg, 4 mmol) is dissolved in a mixture of THF, tBuOH, and water (2:1:1, 60miL). KH2PO4 (1.36 g, 10 mmol) is added followed by NaClO2 (900 mg, 10 mmol). The mixture is stirred at rt for 5 days. Aqueous NaOH (2M, 10 mL) is added and a majority of the organic solvents are removed in vacuo yielding an aqueous suspension. This suspension is diluted with water and washed with three times with CH2Cl2. The aqueous layer is acidified to pH<2 with 25% H2SO4 and the product is extracted three times with CH2Cl2. The combined organic washes are dried over Na2SO4, filtered and concentrated in vacuo to yield 417 mg (51%) of 5-phenylthiophene-2-carboxylic acid. MS for C11H8O2S, (ES) m/z: 203 (M−H)−.

后处理

  1. customa majority of the organic solvents are removed in vacuo
  2. customyielding an aqueous suspension
  3. washwashed with three times with CH2Cl2
  4. extractionthe product is extracted three times with CH2Cl2
  5. dry with materialThe combined organic washes are dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

来源与证据

ORD记录
ord-2d035e661b8c4b5bae83dc4b2ab6c958
来源数据集
uspto-grants-2003_05
专利号
US06562816B2

关联笔记

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